Matteo Colla defeated Maxime Boye 7-5 6-1 in the Italy F10 round of 16 on clay. Matteo Colla extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-21 | Italy 3 Masters 2 | SF | clay | Maxime Boye | 7-6 6-3 |
| 1999-07-12 | France F7 | QF | clay | Matteo Colla | 7-6 6-2 |